ES2383713T3 - Procedimientos para la preparación y el uso de composiciones de quelatos de citrato-pirofosfato férrico - Google Patents

Procedimientos para la preparación y el uso de composiciones de quelatos de citrato-pirofosfato férrico Download PDF

Info

Publication number: ES2383713T3
Authority: ES; Spain
Prior art keywords: pyrophosphate; ferric; citrate; composition; source
Prior art date: 2007-07-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

ES08159949T

Other languages

English (en)

Spanish (es)

Inventor

William S. Mccall Jr.

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Rockwell Medical Inc

Original Assignee

Rockwell Medical Technologies Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2007-07-20

Filing date

2008-07-08

Publication date

2012-06-25

2008-07-08 Application filed by Rockwell Medical Technologies Inc filed Critical Rockwell Medical Technologies Inc

2012-06-25 Application granted granted Critical

2012-06-25 Publication of ES2383713T3 publication Critical patent/ES2383713T3/es

Status Active legal-status Critical Current

2028-07-08 Anticipated expiration legal-status Critical

Links

239000000203 mixture Substances 0.000 title claims abstract description 120
239000013522 chelant Substances 0.000 title claims abstract description 63
235000011180 diphosphates Nutrition 0.000 title claims description 85
238000000034 method Methods 0.000 title claims description 54
229960002413 ferric citrate Drugs 0.000 title claims description 20
NPFOYSMITVOQOS-UHFFFAOYSA-K iron(III) citrate Chemical compound [Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NPFOYSMITVOQOS-UHFFFAOYSA-K 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 79
229910019142 PO4 Inorganic materials 0.000 claims abstract description 39
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 39
239000010452 phosphate Substances 0.000 claims abstract description 39
206010022971 Iron Deficiencies Diseases 0.000 claims abstract description 12
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 133
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 108
229910052742 iron Inorganic materials 0.000 claims description 65
239000007787 solid Substances 0.000 claims description 50
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 49
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 42
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 28
229910001447 ferric ion Inorganic materials 0.000 claims description 27
238000000502 dialysis Methods 0.000 claims description 26
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
239000000463 material Substances 0.000 claims description 21
RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 20
229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
-1 citrate ions Chemical class 0.000 claims description 18
238000004090 dissolution Methods 0.000 claims description 16
DMDVEPIJCJGHPE-UHFFFAOYSA-K azane;2-hydroxypropane-1,2,3-tricarboxylate;iron(3+);hydrate Chemical group N.O.[Fe+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O DMDVEPIJCJGHPE-UHFFFAOYSA-K 0.000 claims description 14
230000008569 process Effects 0.000 claims description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 11
FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 claims description 11
235000019818 tetrasodium diphosphate Nutrition 0.000 claims description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
239000002526 disodium citrate Substances 0.000 claims description 7
235000019262 disodium citrate Nutrition 0.000 claims description 7
CEYULKASIQJZGP-UHFFFAOYSA-L disodium;2-(carboxymethyl)-2-hydroxybutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)CC(O)(C(=O)O)CC([O-])=O CEYULKASIQJZGP-UHFFFAOYSA-L 0.000 claims description 7
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
235000015165 citric acid Nutrition 0.000 claims description 5
239000001509 sodium citrate Substances 0.000 claims description 5
229910052782 aluminium Inorganic materials 0.000 claims description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000006460 hydrolysis reaction Methods 0.000 claims description 4
150000002739 metals Chemical class 0.000 claims description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
230000002829 reductive effect Effects 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
229910052787 antimony Inorganic materials 0.000 claims description 3
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
229910052785 arsenic Inorganic materials 0.000 claims description 3
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
229910052797 bismuth Inorganic materials 0.000 claims description 3
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
229910052793 cadmium Inorganic materials 0.000 claims description 3
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 3
229910052802 copper Inorganic materials 0.000 claims description 3
239000010949 copper Substances 0.000 claims description 3
235000019820 disodium diphosphate Nutrition 0.000 claims description 3
GYQBBRRVRKFJRG-UHFFFAOYSA-L disodium pyrophosphate Chemical compound [Na+].[Na+].OP([O-])(=O)OP(O)([O-])=O GYQBBRRVRKFJRG-UHFFFAOYSA-L 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000006186 oral dosage form Substances 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
229910052716 thallium Inorganic materials 0.000 claims description 3
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 3
229910052718 tin Inorganic materials 0.000 claims description 3
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims description 3
ZOXHEPGCZMYFTR-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;phosphono dihydrogen phosphate Chemical compound OP(O)(=O)OP(O)(O)=O.OC(=O)CC(O)(C(O)=O)CC(O)=O ZOXHEPGCZMYFTR-UHFFFAOYSA-N 0.000 claims description 2
FPFSGDXIBUDDKZ-UHFFFAOYSA-N 3-decyl-2-hydroxycyclopent-2-en-1-one Chemical compound CCCCCCCCCCC1=C(O)C(=O)CC1 FPFSGDXIBUDDKZ-UHFFFAOYSA-N 0.000 claims description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
229910052753 mercury Inorganic materials 0.000 claims description 2
229910052750 molybdenum Inorganic materials 0.000 claims description 2
239000011733 molybdenum Substances 0.000 claims description 2
HWPKGOGLCKPRLZ-UHFFFAOYSA-M monosodium citrate Chemical compound [Na+].OC(=O)CC(O)(C([O-])=O)CC(O)=O HWPKGOGLCKPRLZ-UHFFFAOYSA-M 0.000 claims description 2
239000002524 monosodium citrate Substances 0.000 claims description 2
235000018342 monosodium citrate Nutrition 0.000 claims description 2
229940038773 trisodium citrate Drugs 0.000 claims description 2
235000019263 trisodium citrate Nutrition 0.000 claims description 2
PKDWUXLRYBKARO-UHFFFAOYSA-L 2-hydroxypropane-1,2,3-tricarboxylic acid;iron(2+);phosphono phosphate Chemical compound [Fe+2].OP(O)(=O)OP([O-])([O-])=O.OC(=O)CC(O)(C(O)=O)CC(O)=O PKDWUXLRYBKARO-UHFFFAOYSA-L 0.000 claims 1
150000002500 ions Chemical class 0.000 claims 1
239000006201 parenteral dosage form Substances 0.000 claims 1
SXAWSYZURCZSDX-UHFFFAOYSA-B hydron;[hydroxy(oxido)phosphoryl] hydrogen phosphate;2-hydroxypropane-1,2,3-tricarboxylate;iron(3+);phosphonato phosphate Chemical compound [H+].[H+].[H+].[H+].[H+].[Fe+3].[Fe+3].[Fe+3].[Fe+3].OP([O-])(=O)OP(O)([O-])=O.OP([O-])(=O)OP(O)([O-])=O.[O-]P([O-])(=O)OP([O-])([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O SXAWSYZURCZSDX-UHFFFAOYSA-B 0.000 abstract description 19
150000003839 salts Chemical class 0.000 abstract description 13
235000007144 ferric diphosphate Nutrition 0.000 abstract description 11
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 abstract description 7
239000002552 dosage form Substances 0.000 abstract description 5
150000004676 glycans Chemical class 0.000 abstract description 3
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239000005017 polysaccharide Substances 0.000 abstract description 3
238000007796 conventional method Methods 0.000 abstract 1
229940036417 ferric pyrophosphate citrate Drugs 0.000 abstract 1
229940048084 pyrophosphate Drugs 0.000 description 70
239000000243 solution Substances 0.000 description 56
239000002244 precipitate Substances 0.000 description 29
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208000020832 chronic kidney disease Diseases 0.000 description 8
235000015872 dietary supplement Nutrition 0.000 description 8
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MVZXTUSAYBWAAM-UHFFFAOYSA-N iron;sulfuric acid Chemical compound [Fe].OS(O)(=O)=O MVZXTUSAYBWAAM-UHFFFAOYSA-N 0.000 description 8
238000007254 oxidation reaction Methods 0.000 description 8
OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 8
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239000011706 ferric diphosphate Substances 0.000 description 5
CADNYOZXMIKYPR-UHFFFAOYSA-B ferric pyrophosphate Chemical compound [Fe+3].[Fe+3].[Fe+3].[Fe+3].[O-]P([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])([O-])=O CADNYOZXMIKYPR-UHFFFAOYSA-B 0.000 description 5
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NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 4
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YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/194—Carboxylic acids, e.g. valproic acid having two or more carboxyl groups, e.g. succinic, maleic or phthalic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/28—Compounds containing heavy metals
- A61K31/295—Iron group metal compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/26—Iron; Compounds thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M1/00—Suction or pumping devices for medical purposes; Devices for carrying-off, for treatment of, or for carrying-over, body-liquids; Drainage systems
- A61M1/14—Dialysis systems; Artificial kidneys; Blood oxygenators ; Reciprocating systems for treatment of body fluids, e.g. single needle systems for hemofiltration or pheresis
- A61M1/16—Dialysis systems; Artificial kidneys; Blood oxygenators ; Reciprocating systems for treatment of body fluids, e.g. single needle systems for hemofiltration or pheresis with membranes
- A61M1/1654—Dialysates therefor
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M1/00—Suction or pumping devices for medical purposes; Devices for carrying-off, for treatment of, or for carrying-over, body-liquids; Drainage systems
- A61M1/14—Dialysis systems; Artificial kidneys; Blood oxygenators ; Reciprocating systems for treatment of body fluids, e.g. single needle systems for hemofiltration or pheresis
- A61M1/28—Peritoneal dialysis ; Other peritoneal treatment, e.g. oxygenation
- A61M1/287—Dialysates therefor

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Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Inorganic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Hematology (AREA)
Diabetes (AREA)
Bioinformatics & Cheminformatics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Obesity (AREA)
Nutrition Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Dental Preparations (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

ES08159949T 2007-07-20 2008-07-08 Procedimientos para la preparación y el uso de composiciones de quelatos de citrato-pirofosfato férrico Active ES2383713T3 (es)

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US96132707P	2007-07-20	2007-07-20
US961327P		2007-07-20
US12/138,018 US7816404B2 (en)	2007-07-20	2008-06-12	Methods for the preparation and use of ferric pyrophosphate citrate chelate compositions

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US (1)	US7816404B2 (de)
EP (1)	EP2016940B1 (de)
JP (1)	JP5489196B2 (de)
AT (1)	ATE554754T1 (de)
CY (1)	CY1113903T1 (de)
DK (1)	DK2016940T3 (de)
ES (1)	ES2383713T3 (de)
HR (1)	HRP20120416T1 (de)
PL (1)	PL2016940T3 (de)
PT (1)	PT2016940E (de)
SI (1)	SI2016940T1 (de)

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PT2016940E (pt)	2012-07-12
CY1113903T1 (el)	2016-07-27
HRP20120416T1 (hr)	2012-07-31
JP5489196B2 (ja)	2014-05-14
JP2009108027A (ja)	2009-05-21
PL2016940T3 (pl)	2012-09-28
ATE554754T1 (de)	2012-05-15
EP2016940B1 (de)	2012-04-25
US20090023686A1 (en)	2009-01-22
US7816404B2 (en)	2010-10-19
SI2016940T1 (sl)	2012-07-31
EP2016940A1 (de)	2009-01-21
DK2016940T3 (da)	2012-06-18

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